SU1170972A3 - Способ получени производных 1,1-диоксида 6-аминоалкилпенициллановой кислоты или их аддитивных солей с @ -толуолсульфокислотой - Google Patents

Способ получени производных 1,1-диоксида 6-аминоалкилпенициллановой кислоты или их аддитивных солей с @ -толуолсульфокислотой Download PDF

Info

Publication number: SU1170972A3
Authority: SU; USSR - Soviet Union
Prior art keywords: product; penicillanate; mixture; benzyl; ethyl acetate
Prior art date: 1982-01-11

Application number

SU833534105A

Other languages

English (en)

Russian (ru)

Inventor

Эрнест Барт Вейн

Original Assignee

Пфайзер,Инк.,(Фирма)

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1982-01-11

Filing date

1983-01-10

Publication date

1985-07-30

1982-10-21 Priority claimed from US06/434,371 external-priority patent/US4452796A/en

1983-01-10 Application filed by Пфайзер,Инк.,(Фирма) filed Critical Пфайзер,Инк.,(Фирма)

1985-07-30 Application granted granted Critical

1985-07-30 Publication of SU1170972A3 publication Critical patent/SU1170972A3/ru

Links

238000000034 method Methods 0.000 title claims description 10
150000003839 salts Chemical class 0.000 title claims description 5
239000000654 additive Substances 0.000 title claims 2
230000000996 additive effect Effects 0.000 title claims 2
-1 4-picolyl Chemical group 0.000 claims abstract description 33
239000003054 catalyst Substances 0.000 claims description 13
150000001875 compounds Chemical class 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 7
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 3
238000005984 hydrogenation reaction Methods 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
239000001257 hydrogen Substances 0.000 claims 2
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims 1
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 30
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 4
WYUIPMUZDFHKMP-UHFFFAOYSA-N 5-chloro-1,3-dihydropyrrolo[3,2-b]pyridin-2-one Chemical compound ClC1=CC=C2NC(=O)CC2=N1 WYUIPMUZDFHKMP-UHFFFAOYSA-N 0.000 abstract description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 abstract 1
125000003368 amide group Chemical group 0.000 abstract 1
150000002148 esters Chemical class 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 138
239000000047 product Substances 0.000 description 99
239000000203 mixture Substances 0.000 description 49
229940093499 ethyl acetate Drugs 0.000 description 46
235000019439 ethyl acetate Nutrition 0.000 description 46
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
239000000243 solution Substances 0.000 description 29
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
239000010410 layer Substances 0.000 description 20
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
239000006260 foam Substances 0.000 description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 16
239000000741 silica gel Substances 0.000 description 16
229910002027 silica gel Inorganic materials 0.000 description 16
229960001866 silicon dioxide Drugs 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
239000000706 filtrate Substances 0.000 description 14
239000012044 organic layer Substances 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 11
238000001228 spectrum Methods 0.000 description 11
238000001914 filtration Methods 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
229920006395 saturated elastomer Polymers 0.000 description 7
238000003756 stirring Methods 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 6
239000003480 eluent Substances 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
239000012452 mother liquor Substances 0.000 description 5
RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 description 5
239000012264 purified product Substances 0.000 description 5
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 5
238000005406 washing Methods 0.000 description 5
239000005909 Kieselgur Substances 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000012267 brine Substances 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
239000012071 phase Substances 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000000284 extract Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000012265 solid product Substances 0.000 description 3
ZMMRLWFGWQVVJD-UHFFFAOYSA-O (n,n-dimethylcarbamimidoyl)-dimethylazanium;azide Chemical compound [N-]=[N+]=[N-].CN(C)C(N)=[N+](C)C ZMMRLWFGWQVVJD-UHFFFAOYSA-O 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 2
239000003782 beta lactam antibiotic agent Substances 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
JPOXNPPZZKNXOV-UHFFFAOYSA-N bromochloromethane Chemical compound ClCBr JPOXNPPZZKNXOV-UHFFFAOYSA-N 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000011734 sodium Substances 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
229910021653 sulphate ion Inorganic materials 0.000 description 2
TVZRAEYQIKYCPH-UHFFFAOYSA-N 3-(trimethylsilyl)propane-1-sulfonic acid Chemical compound C[Si](C)(C)CCCS(O)(=O)=O TVZRAEYQIKYCPH-UHFFFAOYSA-N 0.000 description 1
101100404726 Arabidopsis thaliana NHX7 gene Proteins 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
239000007832 Na2SO4 Substances 0.000 description 1
102000057028 SOS1 Human genes 0.000 description 1
108700022176 SOS1 Proteins 0.000 description 1
101100197320 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) RPL35A gene Proteins 0.000 description 1
101100293693 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) STO1 gene Proteins 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
101150100839 Sos1 gene Proteins 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
FAOSYNUKPVJLNZ-UHFFFAOYSA-N butylstannane Chemical compound CCCC[SnH3] FAOSYNUKPVJLNZ-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
101150050497 cbc1 gene Proteins 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
GGRHYQCXXYLUTL-UHFFFAOYSA-N chloromethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCCl GGRHYQCXXYLUTL-UHFFFAOYSA-N 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
230000008014 freezing Effects 0.000 description 1
238000007710 freezing Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000002156 mixing Methods 0.000 description 1
KPADFPAILITQBG-UHFFFAOYSA-N non-4-ene Chemical compound CCCCC=CCCC KPADFPAILITQBG-UHFFFAOYSA-N 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
PZTOXIPENNTIEM-UHFFFAOYSA-N phenylmethoxycarbonylaminomethyl acetate Chemical compound CC(=O)OCNC(=O)OCC1=CC=CC=C1 PZTOXIPENNTIEM-UHFFFAOYSA-N 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000007790 scraping Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000000725 suspension Substances 0.000 description 1
GMRIOAVKKGNMMV-UHFFFAOYSA-N tetrabutylazanium;azide Chemical compound [N-]=[N+]=[N-].CCCC[N+](CCCC)(CCCC)CCCC GMRIOAVKKGNMMV-UHFFFAOYSA-N 0.000 description 1
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
239000002132 β-lactam antibiotic Substances 0.000 description 1
229940124586 β-lactam antibiotics Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
- A61K31/43—Compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula, e.g. penicillins, penems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

SU833534105A 1982-01-11 1983-01-10 Способ получени производных 1,1-диоксида 6-аминоалкилпенициллановой кислоты или их аддитивных солей с @ -толуолсульфокислотой SU1170972A3 (ru)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US33879782A	1982-01-11	1982-01-11
US38832482A	1982-06-14	1982-06-14
US06/434,371 US4452796A (en)	1982-06-14	1982-10-21	6-Aminoalkylpenicillanic acid 1,1-dioxides as beta-lactamase inhibitors

Publications (1)

Publication Number	Publication Date
SU1170972A3 true SU1170972A3 (ru)	1985-07-30

Family

ID=27407295

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU833534105A SU1170972A3 (ru)	1982-01-11	1983-01-10	Способ получени производных 1,1-диоксида 6-аминоалкилпенициллановой кислоты или их аддитивных солей с @ -толуолсульфокислотой

Country Status (3)

Country	Link
KR (1)	KR860001278B1 (cs)
CS (1)	CS268156B2 (cs)
SU (1)	SU1170972A3 (cs)

1983
- 1983-01-07 CS CS83122A patent/CS268156B2/cs unknown
- 1983-01-10 SU SU833534105A patent/SU1170972A3/ru active
- 1983-01-10 KR KR1019830000068A patent/KR860001278B1/ko not_active Expired

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
За вка GB № 2f044255A, кл. С 2 С, опублик. 1980. *

Also Published As

Publication number	Publication date
KR840003256A (ko)	1984-08-20
KR860001278B1 (ko)	1986-09-05
CS268156B2 (en)	1990-03-14
CS12283A2 (en)	1988-08-16

Publication	Publication Date	Title
CA1215708A (en)	1986-12-23	New process for the synthesis of pyrido-imidazo- rifamycins
EP0002210A1 (en)	1979-06-13	6- and 6,6- disubstituted-2-substituted-pen-2-em-3-carboxylic acids; processes for their preparation and pharmaceutical compositions containing such compounds
IE49881B1 (en)	1986-01-08	B-lactam intermediates
JPS6135197B2 (cs)	1986-08-12
EP0181831A2 (de)	1986-05-21	Verfahren zur Herstellung von optisch aktiven Acyloxyazetidinonen
DE2258221C2 (de)	1981-10-08	Verfahren zur Herstellung von Penicillinen und Cepholosporinen mit einem weiteren Substituenten in 6- bzw. 7-Stellung
EP0013617B1 (en)	1984-07-04	Penicillin derivatives, process for their preparation and pharmaceutical compositions containing certain of these compounds
US4296236A (en)	1981-10-20	7-(or 6-) Substituted-7-(or 6-)acylimino cephalosporin (or penicillin) compounds
EP0114752B1 (en)	1988-04-06	Beta-lactam antibacterial agents
CA1281713C (en)	1991-03-19	Process for preparing new penem compounds
US4468351A (en)	1984-08-28	Process for debromination of dibromopenicillanic acid and derivatives
DE3344317C2 (cs)	1992-02-27
SU1170972A3 (ru)	1985-07-30	Способ получени производных 1,1-диоксида 6-аминоалкилпенициллановой кислоты или их аддитивных солей с @ -толуолсульфокислотой
CA1275405C (en)	1990-10-23	Penem derivatives
CA1271742A (en)	1990-07-17	Penem derivatives
US3862182A (en)	1975-01-21	Process to prepare novel antibiotic intermediates
NO164031B (no)	1990-05-14	Fremgangsm te for fremstilling av beta-laktamer.
FI79112C (fi)	1989-11-10	6-aminoalkylpenicillansyra-1,1-dioxider och deras derivat som -laktamas-inhibitorer.
US4356122A (en)	1982-10-26	6-Perhaloalkylsulfonyloxy-penicillanic acids and derivatives thereof
EP0003415A2 (en)	1979-08-08	Beta-Lactam compounds, processes for their preparation,compositions containing them and intermediates of use in their preparation
DE2550867C2 (de)	1984-08-23	Verfahren zur Herstellung von 7&beta;-Benzylidenamino-7&alpha;-methoxy-3-cephem-Verbindungen
JPH0247996B2 (cs)	1990-10-23
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